4-Methylmorpholine → HCID 60019683, compound

HRID 604826Notes

Reaction equation

HRID 604826 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][OH:12])=[CH:2]1.CN1CCOCC1.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:22]>O>[N+:30]([C:27]1[CH:26]=[CH:25][C:24]([O:23][C:21](=[O:22])[O:12][CH2:11][CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[CH:29][CH:28]=1)([O-:32])=[O:31]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 10685TryptopholHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 60019683HCID 60019683, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(1H-indol-3-yl)-ethanol (1600 mg, 9.92 mmol), in N-methyl morpholine (2000 m g, 19.84 mmol), was added p-nitrophenyl chloroformate (4000 mg, 19.84 mmol), and the mixture was stirred for 24 hours at room temperature. Water was added and the mixture extracted with dichloromethane. Evaporation of the solvent gave a residue which was purified by silica gel column chromatography using a mixture of DCM/Hx (3:1) as eluent to produce 1034 mg (32%) of the title compound as a yellow solid.

Workup

  1. extractionthe mixture extracted with dichloromethane
  2. customEvaporation of the solvent
  3. customgave a residue which
  4. customwas purified by silica gel column chromatography
  5. additiona mixture of DCM/Hx (3:1) as eluent

Sources & evidence

ORD record
ord-730f71b609334eadac6a37e188b2f64f
Source dataset
uspto-grants-2011_03
Patent number
US07910739B2

Reaction notes

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